NZ543482A - Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phoshorylase - Google Patents

Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phoshorylase

Info

Publication number: NZ543482A
Authority: NZ; New Zealand
Prior art keywords: 4alkyl; chloro; carboxylic acid; preparation; pyridine
Prior art date: 2003-05-21

Application number

NZ543482A

Other languages

English (en)

Inventor

Stuart Edward Bradley

Thomas Martin Krulle

Peter John Murray

Martin James Procter

Robert John Rowley

Smith Colin Peter Sambrook

Gerard Hugh Thomas

Karen Lesley Schofield

Original Assignee

Prosidion Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-05-21

Filing date

2004-05-20

Publication date

2009-02-28

2004-05-20 Application filed by Prosidion Ltd filed Critical Prosidion Ltd

2009-02-28 Publication of NZ543482A publication Critical patent/NZ543482A/en

Links

239000003112 inhibitor Substances 0.000 title description 22
229920002527 Glycogen Polymers 0.000 title description 5
229940096919 glycogen Drugs 0.000 title description 5
YWHNNPXTZCBOJQ-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=N1 YWHNNPXTZCBOJQ-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 479
150000003839 salts Chemical class 0.000 claims abstract description 74
238000011282 treatment Methods 0.000 claims abstract description 19
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 12
238000004519 manufacturing process Methods 0.000 claims abstract description 8
239000003814 drug Substances 0.000 claims abstract description 6
230000005961 cardioprotection Effects 0.000 claims abstract description 3
230000002265 prevention Effects 0.000 claims abstract description 3
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 163
239000002253 acid Substances 0.000 claims description 115
239000000203 mixture Substances 0.000 claims description 113
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 74
-1 hydroxy, fluoromethyl Chemical group 0.000 claims description 73
238000006243 chemical reaction Methods 0.000 claims description 69
238000000034 method Methods 0.000 claims description 50
125000000623 heterocyclic group Chemical group 0.000 claims description 34
229910052736 halogen Inorganic materials 0.000 claims description 30
229910052757 nitrogen Inorganic materials 0.000 claims description 30
150000002367 halogens Chemical class 0.000 claims description 28
125000004093 cyano group Chemical group *C#N 0.000 claims description 27
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
150000001412 amines Chemical class 0.000 claims description 23
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 20
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 19
MYDSAMPAYOLUMG-UHFFFAOYSA-N 3-aminothieno[3,2-b]pyridine-2-carboxylic acid Chemical compound C1=CN=C2C(N)=C(C(O)=O)SC2=C1 MYDSAMPAYOLUMG-UHFFFAOYSA-N 0.000 claims description 18
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
125000003118 aryl group Chemical group 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 14
230000008878 coupling Effects 0.000 claims description 14
238000010168 coupling process Methods 0.000 claims description 14
238000005859 coupling reaction Methods 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
125000001072 heteroaryl group Chemical group 0.000 claims description 13
229910052727 yttrium Inorganic materials 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 10
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
239000003937 drug carrier Substances 0.000 claims description 9
201000001421 hyperglycemia Diseases 0.000 claims description 9
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
201000001320 Atherosclerosis Diseases 0.000 claims description 8
208000035150 Hypercholesterolemia Diseases 0.000 claims description 8
206010060378 Hyperinsulinaemia Diseases 0.000 claims description 8
208000031226 Hyperlipidaemia Diseases 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
230000003451 hyperinsulinaemic effect Effects 0.000 claims description 8
201000008980 hyperinsulinism Diseases 0.000 claims description 8
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
208000031225 myocardial ischemia Diseases 0.000 claims description 7
230000001225 therapeutic effect Effects 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
230000000069 prophylactic effect Effects 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
150000002431 hydrogen Chemical group 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
KBHQUFPZXCNYKN-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=N1 KBHQUFPZXCNYKN-UHFFFAOYSA-N 0.000 claims description 3
VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims description 3
208000002705 Glucose Intolerance Diseases 0.000 claims description 3
XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 claims description 3
238000003556 assay Methods 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
150000001735 carboxylic acids Chemical class 0.000 claims description 3
238000010931 ester hydrolysis Methods 0.000 claims description 3
125000001475 halogen functional group Chemical group 0.000 claims description 3
230000005764 inhibitory process Effects 0.000 claims description 3
DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 claims description 3
201000009104 prediabetes syndrome Diseases 0.000 claims description 3
ARAFEULRMHFMDE-UHFFFAOYSA-N 1,3-oxazolidine-2,5-dione Chemical compound O=C1CNC(=O)O1 ARAFEULRMHFMDE-UHFFFAOYSA-N 0.000 claims description 2
101100134925 Gallus gallus COR6 gene Proteins 0.000 claims description 2
206010018429 Glucose tolerance impaired Diseases 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
231100000673 dose–response relationship Toxicity 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 537
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 377
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 362
238000002360 preparation method Methods 0.000 description 301
239000000243 solution Substances 0.000 description 270
235000019439 ethyl acetate Nutrition 0.000 description 183
239000007787 solid Substances 0.000 description 169
229910001868 water Inorganic materials 0.000 description 160
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 155
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 132
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 125
239000002904 solvent Substances 0.000 description 122
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 121
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 114
239000012267 brine Substances 0.000 description 94
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 94
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 92
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 88
239000011541 reaction mixture Substances 0.000 description 88
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 85
150000001408 amides Chemical class 0.000 description 84
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 82
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 80
238000000746 purification Methods 0.000 description 69
238000004587 chromatography analysis Methods 0.000 description 62
239000000741 silica gel Substances 0.000 description 61
229910002027 silica gel Inorganic materials 0.000 description 61
229910052943 magnesium sulfate Inorganic materials 0.000 description 59
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 53
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 52
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 48
239000000843 powder Substances 0.000 description 47
239000010410 layer Substances 0.000 description 45
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 41
239000000460 chlorine Substances 0.000 description 38
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 37
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 34
239000003921 oil Substances 0.000 description 31
238000003756 stirring Methods 0.000 description 31
229960000583 acetic acid Drugs 0.000 description 30
238000003818 flash chromatography Methods 0.000 description 30
235000019198 oils Nutrition 0.000 description 30
239000000725 suspension Substances 0.000 description 30
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 29
108010046163 Glycogen Phosphorylase Proteins 0.000 description 29
102000007390 Glycogen Phosphorylase Human genes 0.000 description 29
239000003480 eluent Substances 0.000 description 29
238000010992 reflux Methods 0.000 description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
239000000047 product Substances 0.000 description 27
239000012044 organic layer Substances 0.000 description 26
239000002244 precipitate Substances 0.000 description 26
238000005406 washing Methods 0.000 description 26
239000013058 crude material Substances 0.000 description 23
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 20
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 20
239000000284 extract Substances 0.000 description 20
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 19
238000001914 filtration Methods 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
239000008346 aqueous phase Substances 0.000 description 17
229910052786 argon Inorganic materials 0.000 description 17
101150041968 CDC13 gene Proteins 0.000 description 15
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
238000001035 drying Methods 0.000 description 14
239000000706 filtrate Substances 0.000 description 14
229920006395 saturated elastomer Polymers 0.000 description 14
238000000605 extraction Methods 0.000 description 13
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 13
239000008194 pharmaceutical composition Substances 0.000 description 13
RJNUXEDAPIKMDE-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride;hydrate Chemical compound O.[Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 RJNUXEDAPIKMDE-UHFFFAOYSA-M 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 11
239000012362 glacial acetic acid Substances 0.000 description 11
LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 11
230000002829 reductive effect Effects 0.000 description 11
239000004480 active ingredient Substances 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
238000004440 column chromatography Methods 0.000 description 10
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
FQYYIPZPELSLDK-UHFFFAOYSA-N ethyl pyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=CC=N1 FQYYIPZPELSLDK-UHFFFAOYSA-N 0.000 description 10
239000007788 liquid Substances 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
239000012317 TBTU Substances 0.000 description 9
CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
238000001665 trituration Methods 0.000 description 9
239000003039 volatile agent Substances 0.000 description 9
MIJRRMLODIKPEA-UHFFFAOYSA-N 5-chloro-1h-pyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound ClC1=NC=C2NC(C(=O)O)=CC2=C1 MIJRRMLODIKPEA-UHFFFAOYSA-N 0.000 description 8
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 8
239000012300 argon atmosphere Substances 0.000 description 8
239000002585 base Substances 0.000 description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 8
238000002953 preparative HPLC Methods 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 7
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
150000003927 aminopyridines Chemical class 0.000 description 7
239000000969 carrier Substances 0.000 description 7
201000010099 disease Diseases 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
231100000252 nontoxic Toxicity 0.000 description 7
230000003000 nontoxic effect Effects 0.000 description 7
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
206010020772 Hypertension Diseases 0.000 description 6
102000004877 Insulin Human genes 0.000 description 6
108090001061 Insulin Proteins 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
239000006071 cream Substances 0.000 description 6
NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 6
229940125396 insulin Drugs 0.000 description 6
229910052740 iodine Inorganic materials 0.000 description 6
239000011630 iodine Substances 0.000 description 6
239000000463 material Substances 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
239000003826 tablet Substances 0.000 description 6
LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical compound NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
235000019270 ammonium chloride Nutrition 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
239000012043 crude product Substances 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
125000004122 cyclic group Chemical group 0.000 description 5
XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 5
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
208000028867 ischemia Diseases 0.000 description 5
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
229950009215 phenylbutanoic acid Drugs 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
108090000765 processed proteins & peptides Proteins 0.000 description 5
235000019260 propionic acid Nutrition 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 5
235000019345 sodium thiosulphate Nutrition 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
239000011593 sulfur Substances 0.000 description 5
210000001519 tissue Anatomy 0.000 description 5
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
239000005557 antagonist Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
239000008280 blood Substances 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
230000037396 body weight Effects 0.000 description 4
239000002775 capsule Substances 0.000 description 4
230000005595 deprotonation Effects 0.000 description 4
238000010537 deprotonation reaction Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
125000004494 ethyl ester group Chemical group 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 4
FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
229940107700 pyruvic acid Drugs 0.000 description 4
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
235000000346 sugar Nutrition 0.000 description 4
PXCPSDYQUKLPPQ-UHFFFAOYSA-N tert-butyl 2-amino-2h-pyridine-1-carboxylate Chemical class CC(C)(C)OC(=O)N1C=CC=CC1N PXCPSDYQUKLPPQ-UHFFFAOYSA-N 0.000 description 4
KHWYSUBVXWWBRB-UHFFFAOYSA-N (+/-)-n-ethyl-1-phenyl-2-butylamine Chemical compound CCNC(CC)CC1=CC=CC=C1 KHWYSUBVXWWBRB-UHFFFAOYSA-N 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
VJRXDPNRSQWHRH-ZDUSSCGKSA-N (2s)-2-[(5-chloro-1h-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1NC2=CN=C(Cl)C=C2C=1)C1=CC=C(F)C=C1 VJRXDPNRSQWHRH-ZDUSSCGKSA-N 0.000 description 3
RDPRSYDIZANKLQ-ZDUSSCGKSA-N (2s)-2-[(5-chloro-1h-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1NC2=CN=C(Cl)C=C2C=1)C1=CC=CC=C1 RDPRSYDIZANKLQ-ZDUSSCGKSA-N 0.000 description 3
JHHZLHWJQPUNKB-BYPYZUCNSA-N (3s)-pyrrolidin-3-ol Chemical compound O[C@H]1CCNC1 JHHZLHWJQPUNKB-BYPYZUCNSA-N 0.000 description 3
UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 3
NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 3
GBBSAMQTQCPOBF-UHFFFAOYSA-N 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane Chemical compound CB1OB(C)OB(C)O1 GBBSAMQTQCPOBF-UHFFFAOYSA-N 0.000 description 3
HWZUMEVIIGNXGM-UHFFFAOYSA-N 2-chloro-4-methyl-5-nitropyridine Chemical compound CC1=CC(Cl)=NC=C1[N+]([O-])=O HWZUMEVIIGNXGM-UHFFFAOYSA-N 0.000 description 3
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 3
CCFGTKQIRWHYTB-UHFFFAOYSA-N 2-methyl-3-nitropyridine Chemical compound CC1=NC=CC=C1[N+]([O-])=O CCFGTKQIRWHYTB-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
239000000556 agonist Substances 0.000 description 3
229960003767 alanine Drugs 0.000 description 3
239000003472 antidiabetic agent Substances 0.000 description 3
UQUPQEUNHVVNKW-UHFFFAOYSA-N azetidin-1-ium-3-ol;chloride Chemical compound Cl.OC1CNC1 UQUPQEUNHVVNKW-UHFFFAOYSA-N 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
125000002837 carbocyclic group Chemical group 0.000 description 3
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000007822 coupling agent Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
230000001419 dependent effect Effects 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000008103 glucose Substances 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
229940126904 hypoglycaemic agent Drugs 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000000314 lubricant Substances 0.000 description 3
FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 3
229940107698 malachite green Drugs 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
OCIDXARMXNJACB-UHFFFAOYSA-N n'-phenylethane-1,2-diamine Chemical compound NCCNC1=CC=CC=C1 OCIDXARMXNJACB-UHFFFAOYSA-N 0.000 description 3
239000002674 ointment Substances 0.000 description 3
125000001979 organolithium group Chemical group 0.000 description 3
CVXGFPPAIUELDV-UHFFFAOYSA-N phenacylazanium;chloride Chemical compound [Cl-].[NH3+]CC(=O)C1=CC=CC=C1 CVXGFPPAIUELDV-UHFFFAOYSA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000010791 quenching Methods 0.000 description 3
230000000171 quenching effect Effects 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000012453 solvate Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
RZPXITSRAQPKRU-UHFFFAOYSA-N tert-butyl n-(3-methylpyridin-4-yl)carbamate Chemical compound CC1=CN=CC=C1NC(=O)OC(C)(C)C RZPXITSRAQPKRU-UHFFFAOYSA-N 0.000 description 3
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 3
229960000281 trometamol Drugs 0.000 description 3
ZYJPUMXJBDHSIF-NSHDSACASA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 ZYJPUMXJBDHSIF-NSHDSACASA-N 0.000 description 2
NTFPAOHCUPWJNQ-PPHPATTJSA-N (2s)-2-amino-n,n-dimethyl-3-phenylpropanamide;hydrochloride Chemical compound Cl.CN(C)C(=O)[C@@H](N)CC1=CC=CC=C1 NTFPAOHCUPWJNQ-PPHPATTJSA-N 0.000 description 2
SQMYKVUSWPIFEQ-NUBCRITNSA-N (3r)-3-methoxypyrrolidine;hydrochloride Chemical compound Cl.CO[C@@H]1CCNC1 SQMYKVUSWPIFEQ-NUBCRITNSA-N 0.000 description 2
JCZPOYAMKJFOLA-ZXZARUISSA-N (3s,4r)-pyrrolidine-3,4-diol Chemical compound O[C@H]1CNC[C@H]1O JCZPOYAMKJFOLA-ZXZARUISSA-N 0.000 description 2
FUXSSMSAWSOUSN-QMMMGPOBSA-N (4s)-4-[(4-fluorophenyl)methyl]-1,3-oxazolidine-2,5-dione Chemical compound C1=CC(F)=CC=C1C[C@H]1C(=O)OC(=O)N1 FUXSSMSAWSOUSN-QMMMGPOBSA-N 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
PWWYFIZEQHFRJH-UHFFFAOYSA-N 1h-pyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound C1=NC=C2NC(C(=O)O)=CC2=C1 PWWYFIZEQHFRJH-UHFFFAOYSA-N 0.000 description 2
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
GMAJNANLBOHCAU-UHFFFAOYSA-N 2,4-dimethyl-5-nitropyridine Chemical compound CC1=CC(C)=C([N+]([O-])=O)C=N1 GMAJNANLBOHCAU-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 2
BTKNUYMZBBWHIM-UHFFFAOYSA-N 2-amino-1-pyridin-3-ylethanol Chemical compound NCC(O)C1=CC=CN=C1 BTKNUYMZBBWHIM-UHFFFAOYSA-N 0.000 description 2
OSYUAHGEDKTDOX-UHFFFAOYSA-N 2-bromo-4-methyl-5-nitropyridine Chemical compound CC1=CC(Br)=NC=C1[N+]([O-])=O OSYUAHGEDKTDOX-UHFFFAOYSA-N 0.000 description 2
JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 2
AXCYYSJUKJGMHN-UHFFFAOYSA-N 4-(2-methoxyethoxy)piperidine-1-carboxylic acid Chemical compound COCCOC1CCN(C(O)=O)CC1 AXCYYSJUKJGMHN-UHFFFAOYSA-N 0.000 description 2
KIHBPEJNVKMUOV-UHFFFAOYSA-N 4-(2-methoxyethoxy)piperidine;hydrochloride Chemical compound Cl.COCCOC1CCNCC1 KIHBPEJNVKMUOV-UHFFFAOYSA-N 0.000 description 2
DMFJRRMECZFOKR-UHFFFAOYSA-N 4-methoxypiperidine;hydrochloride Chemical compound Cl.COC1CCNCC1 DMFJRRMECZFOKR-UHFFFAOYSA-N 0.000 description 2
GHSRMSJVYMITDX-UHFFFAOYSA-N 6-chloro-2-methyl-3-nitropyridine Chemical compound CC1=NC(Cl)=CC=C1[N+]([O-])=O GHSRMSJVYMITDX-UHFFFAOYSA-N 0.000 description 2
GGXIOSCUHASSOL-UHFFFAOYSA-N 6-chloro-3-iodopyridin-2-amine Chemical compound NC1=NC(Cl)=CC=C1I GGXIOSCUHASSOL-UHFFFAOYSA-N 0.000 description 2
UOICMMKVFPTQMX-UHFFFAOYSA-N 6-chloro-4-iodopyridin-3-amine Chemical compound NC1=CN=C(Cl)C=C1I UOICMMKVFPTQMX-UHFFFAOYSA-N 0.000 description 2
GSJQJZOENXJWIP-UHFFFAOYSA-N 6-methoxy-2-methyl-3-nitropyridine Chemical compound COC1=CC=C([N+]([O-])=O)C(C)=N1 GSJQJZOENXJWIP-UHFFFAOYSA-N 0.000 description 2
ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
235000019502 Orange oil Nutrition 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
206010063837 Reperfusion injury Diseases 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
230000002411 adverse Effects 0.000 description 2
239000003513 alkali Substances 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
HXXFSFRBOHSIMQ-VFUOTHLCSA-N alpha-D-glucose 1-phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O HXXFSFRBOHSIMQ-VFUOTHLCSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
239000006286 aqueous extract Substances 0.000 description 2
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
239000012455 biphasic mixture Substances 0.000 description 2
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000010949 copper Substances 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
235000005911 diet Nutrition 0.000 description 2
230000037213 diet Effects 0.000 description 2
WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 2
238000000132 electrospray ionisation Methods 0.000 description 2
FPFQPLFYTKMCHN-PPHPATTJSA-N ethyl (2s)-2-amino-3-phenylpropanoate;hydron;chloride Chemical compound Cl.CCOC(=O)[C@@H](N)CC1=CC=CC=C1 FPFQPLFYTKMCHN-PPHPATTJSA-N 0.000 description 2
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 2
WTFZXUWGQQRKPX-UHFFFAOYSA-N ethyl 3-(2-bromo-5-nitropyridin-4-yl)-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CC1=CC(Br)=NC=C1[N+]([O-])=O WTFZXUWGQQRKPX-UHFFFAOYSA-N 0.000 description 2
QMPFDBOEONYNNO-UHFFFAOYSA-N ethyl 3-(2-chloro-5-nitropyridin-4-yl)-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CC1=CC(Cl)=NC=C1[N+]([O-])=O QMPFDBOEONYNNO-UHFFFAOYSA-N 0.000 description 2
LLMOHNWYDHSUJB-UHFFFAOYSA-N ethyl 3-(3-nitropyridin-2-yl)-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CC1=NC=CC=C1[N+]([O-])=O LLMOHNWYDHSUJB-UHFFFAOYSA-N 0.000 description 2
UQTZFCLLZIWSLZ-UHFFFAOYSA-N ethyl 3-(6-chloro-3-nitropyridin-2-yl)-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CC1=NC(Cl)=CC=C1[N+]([O-])=O UQTZFCLLZIWSLZ-UHFFFAOYSA-N 0.000 description 2
ABZYRRKHJXRBDH-UHFFFAOYSA-N ethyl 3-(6-methoxy-3-nitropyridin-2-yl)-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CC1=NC(OC)=CC=C1[N+]([O-])=O ABZYRRKHJXRBDH-UHFFFAOYSA-N 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000006260 foam Substances 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
239000012458 free base Substances 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
230000009229 glucose formation Effects 0.000 description 2
229950010772 glucose-1-phosphate Drugs 0.000 description 2
239000008187 granular material Substances 0.000 description 2
230000002440 hepatic effect Effects 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000011534 incubation Methods 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
JNODQFNWMXFMEV-UHFFFAOYSA-N latrepirdine Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1 JNODQFNWMXFMEV-UHFFFAOYSA-N 0.000 description 2
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
XAVNWNCTXQDFLF-UHFFFAOYSA-N methyl piperidin-1-ium-4-carboxylate;chloride Chemical compound Cl.COC(=O)C1CCNCC1 XAVNWNCTXQDFLF-UHFFFAOYSA-N 0.000 description 2
MMMCYLTUYKZCEN-UHFFFAOYSA-N methyl(oxan-4-yl)azanium;chloride Chemical compound Cl.CNC1CCOCC1 MMMCYLTUYKZCEN-UHFFFAOYSA-N 0.000 description 2
244000005700 microbiome Species 0.000 description 2
238000000465 moulding Methods 0.000 description 2
210000003205 muscle Anatomy 0.000 description 2
YFJAIURZMRJPDB-UHFFFAOYSA-N n,n-dimethylpiperidin-4-amine Chemical compound CN(C)C1CCNCC1 YFJAIURZMRJPDB-UHFFFAOYSA-N 0.000 description 2
WLKJVLXONNQXSE-UHFFFAOYSA-N n-(2-phenylethyl)oxan-4-amine Chemical compound C1COCCC1NCCC1=CC=CC=C1 WLKJVLXONNQXSE-UHFFFAOYSA-N 0.000 description 2
SAQCDMGMWAACSN-UHFFFAOYSA-N n-(6-chloro-3-iodopyridin-2-yl)-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=NC(Cl)=CC=C1I SAQCDMGMWAACSN-UHFFFAOYSA-N 0.000 description 2
YPWKLBCTOUEZKE-UHFFFAOYSA-N n-(6-chloropyridin-2-yl)-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC=CC(Cl)=N1 YPWKLBCTOUEZKE-UHFFFAOYSA-N 0.000 description 2
NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 2
239000010502 orange oil Substances 0.000 description 2
AHVQYHFYQWKUKB-UHFFFAOYSA-N oxan-4-amine Chemical compound NC1CCOCC1 AHVQYHFYQWKUKB-UHFFFAOYSA-N 0.000 description 2
230000009038 pharmacological inhibition Effects 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
230000035479 physiological effects, processes and functions Effects 0.000 description 2
229920000768 polyamine Polymers 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
102000004196 processed proteins & peptides Human genes 0.000 description 2
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 2
CJIVCSBYIRBJSG-UHFFFAOYSA-N pyrrolidine-3,3-diol Chemical compound OC1(O)CCNC1 CJIVCSBYIRBJSG-UHFFFAOYSA-N 0.000 description 2
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
239000000018 receptor agonist Substances 0.000 description 2
229940044601 receptor agonist Drugs 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
239000003001 serine protease inhibitor Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
IKBGJVQIHZGXTH-UHFFFAOYSA-N tert-butyl 4-[(2-nitrophenyl)sulfonylamino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O IKBGJVQIHZGXTH-UHFFFAOYSA-N 0.000 description 2
LZRDHSFPLUWYAX-UHFFFAOYSA-N tert-butyl 4-aminopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)CC1 LZRDHSFPLUWYAX-UHFFFAOYSA-N 0.000 description 2
WATASAJREKAPOT-UHFFFAOYSA-N tert-butyl 4-methoxypiperidine-1-carboxylate Chemical compound COC1CCN(C(=O)OC(C)(C)C)CC1 WATASAJREKAPOT-UHFFFAOYSA-N 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
239000003643 water by type Substances 0.000 description 2
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
UZNMTXBFUKJYFH-UHFFFAOYSA-N (1h-indol-2-ylamino)thiourea Chemical class C1=CC=C2NC(NNC(=S)N)=CC2=C1 UZNMTXBFUKJYFH-UHFFFAOYSA-N 0.000 description 1
TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 1
DOMQFIFVDIAOOT-ROUUACIJSA-N (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NN=C1C=1C=NC=C(C=1)C)NS(=O)(=O)[C@@H](C)[C@H](C)C1=NC=C(C=N1)C DOMQFIFVDIAOOT-ROUUACIJSA-N 0.000 description 1
JQAOHGMPAAWWQO-QMMMGPOBSA-N (2s)-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CCCC[C@H]1C(O)=O JQAOHGMPAAWWQO-QMMMGPOBSA-N 0.000 description 1
FLFQHYCHCVUFAA-AWEZNQCLSA-N (2s)-2-[(5-chloro-1h-pyrrolo[2,3-b]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1NC2=NC=C(Cl)C=C2C=1)C1=CC=C(F)C=C1 FLFQHYCHCVUFAA-AWEZNQCLSA-N 0.000 description 1
RQJJEGJZWPMPHM-MERQFXBCSA-N (2s)-2-amino-3-pyridin-3-yl-1-pyrrolidin-1-ylpropan-1-one;hydrochloride Chemical compound Cl.C([C@H](N)C(=O)N1CCCC1)C1=CC=CN=C1 RQJJEGJZWPMPHM-MERQFXBCSA-N 0.000 description 1
RCXSXRAUMLKRRL-NSHDSACASA-N (2s)-3-(4-fluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC1=CC=C(F)C=C1 RCXSXRAUMLKRRL-NSHDSACASA-N 0.000 description 1
SQMYKVUSWPIFEQ-JEDNCBNOSA-N (3s)-3-methoxypyrrolidine;hydrochloride Chemical compound Cl.CO[C@H]1CCNC1 SQMYKVUSWPIFEQ-JEDNCBNOSA-N 0.000 description 1
JWKSNJFIXPHHEZ-UHFFFAOYSA-N (6-chloro-4-iodopyridin-3-yl)carbamic acid Chemical compound OC(=O)NC1=CN=C(Cl)C=C1I JWKSNJFIXPHHEZ-UHFFFAOYSA-N 0.000 description 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 description 1
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
HEAHLTGDUHXTTO-UHFFFAOYSA-N 1,3-thiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCNC1 HEAHLTGDUHXTTO-UHFFFAOYSA-N 0.000 description 1
KZPUZEPLLNUDDZ-UHFFFAOYSA-N 1,3-thiazolidine 1-oxide Chemical compound O=S1CCNC1 KZPUZEPLLNUDDZ-UHFFFAOYSA-N 0.000 description 1
FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
KPKNTUUIEVXMOH-UHFFFAOYSA-N 1,4-dioxa-8-azaspiro[4.5]decane Chemical compound O1CCOC11CCNCC1 KPKNTUUIEVXMOH-UHFFFAOYSA-N 0.000 description 1
YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 description 1
YUBDLZGUSSWQSS-UHFFFAOYSA-N 1-benzylpiperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CC=C1 YUBDLZGUSSWQSS-UHFFFAOYSA-N 0.000 description 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
WSWPCNMLEVZGSM-UHFFFAOYSA-N 2-(2-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC=C1CCN WSWPCNMLEVZGSM-UHFFFAOYSA-N 0.000 description 1
CKLFJWXRWIQYOC-UHFFFAOYSA-N 2-(4-fluorophenyl)ethanamine Chemical compound NCCC1=CC=C(F)C=C1 CKLFJWXRWIQYOC-UHFFFAOYSA-N 0.000 description 1
YXRCDWIZAGWUBL-UHFFFAOYSA-N 2-(4-methoxyphenoxy)ethanamine Chemical compound COC1=CC=C(OCCN)C=C1 YXRCDWIZAGWUBL-UHFFFAOYSA-N 0.000 description 1
KNNHPOGBBNRNDH-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]ethanamine Chemical compound NCCSCC1=C(F)C=CC=C1Cl KNNHPOGBBNRNDH-UHFFFAOYSA-N 0.000 description 1
ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 1
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
XQJAHBHCLXUGEP-UHFFFAOYSA-N 2-bromo-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)CBr)C=C1 XQJAHBHCLXUGEP-UHFFFAOYSA-N 0.000 description 1
IQMGXSROJBYCLS-UHFFFAOYSA-N 2-bromo-1-pyridin-3-ylethanone Chemical compound BrCC(=O)C1=CC=CN=C1 IQMGXSROJBYCLS-UHFFFAOYSA-N 0.000 description 1
UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 description 1
DEJUUKULVAIMNF-UHFFFAOYSA-N 2-chloro-5-iodopyridin-4-amine Chemical compound NC1=CC(Cl)=NC=C1I DEJUUKULVAIMNF-UHFFFAOYSA-N 0.000 description 1
DVRGUTNVDGIKTP-UHFFFAOYSA-N 2-chloro-6-methoxy-3-nitropyridine Chemical compound COC1=CC=C([N+]([O-])=O)C(Cl)=N1 DVRGUTNVDGIKTP-UHFFFAOYSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
229940013085 2-diethylaminoethanol Drugs 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
WBBPRCNXBQTYLF-UHFFFAOYSA-N 2-methylthioethanol Chemical compound CSCCO WBBPRCNXBQTYLF-UHFFFAOYSA-N 0.000 description 1
UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 1
IRTLROCMFSDSNF-UHFFFAOYSA-N 2-phenyl-1h-pyrrole Chemical class C1=CNC(C=2C=CC=CC=2)=C1 IRTLROCMFSDSNF-UHFFFAOYSA-N 0.000 description 1
HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical compound NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 description 1
HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
ZMKXWDPUXLPHCA-UHFFFAOYSA-N 3-(4-fluorophenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(F)C=C1 ZMKXWDPUXLPHCA-UHFFFAOYSA-N 0.000 description 1
AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical class OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 description 1
FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 description 1
BXGFHCNYQWPVDQ-UHFFFAOYSA-N 4-(2-phenylethylamino)piperidine-1-carboxylic acid Chemical compound C1CN(CCC1NCCC2=CC=CC=C2)C(=O)O BXGFHCNYQWPVDQ-UHFFFAOYSA-N 0.000 description 1
WXGIHEMNGKCOGU-UHFFFAOYSA-N 4-(3-methoxypropoxy)piperidine;hydrochloride Chemical compound Cl.COCCCOC1CCNCC1 WXGIHEMNGKCOGU-UHFFFAOYSA-N 0.000 description 1
HHEPTRCSBLYPFS-UHFFFAOYSA-N 4-(methanesulfonamido)piperidine-1-carboxylic acid Chemical compound CS(=O)(=O)NC1CCN(C(O)=O)CC1 HHEPTRCSBLYPFS-UHFFFAOYSA-N 0.000 description 1
CYKQBISFMXUEBJ-UHFFFAOYSA-N 4-(methylamino)piperidine-1-carboxylic acid Chemical compound CNC1CCN(C(O)=O)CC1 CYKQBISFMXUEBJ-UHFFFAOYSA-N 0.000 description 1
RDRQUUWCJTYHCT-UHFFFAOYSA-N 4-(trifluoromethyl)piperidine Chemical compound FC(F)(F)C1CCNCC1 RDRQUUWCJTYHCT-UHFFFAOYSA-N 0.000 description 1
BLBDTBCGPHPIJK-UHFFFAOYSA-N 4-Amino-2-chloropyridine Chemical compound NC1=CC=NC(Cl)=C1 BLBDTBCGPHPIJK-UHFFFAOYSA-N 0.000 description 1
KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
XWHHYOYVRVGJJY-QMMMGPOBSA-N 4-fluoro-L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(F)C=C1 XWHHYOYVRVGJJY-QMMMGPOBSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
AIEHUZHKFUNHCJ-UHFFFAOYSA-N 4-methyl-5-nitro-1h-pyridin-2-one Chemical compound CC1=CC(O)=NC=C1[N+]([O-])=O AIEHUZHKFUNHCJ-UHFFFAOYSA-N 0.000 description 1
YMSGAOPCRLRFMT-UHFFFAOYSA-N 5-chloro-1h-pyrrolo[2,3-b]pyridine-2-carboxylic acid Chemical compound ClC1=CN=C2NC(C(=O)O)=CC2=C1 YMSGAOPCRLRFMT-UHFFFAOYSA-N 0.000 description 1
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
DIONPYCYVWCDIG-UHFFFAOYSA-N 5-chloro-3-iodopyridin-2-amine Chemical compound NC1=NC=C(Cl)C=C1I DIONPYCYVWCDIG-UHFFFAOYSA-N 0.000 description 1
ATAGKZOABSLIMT-UHFFFAOYSA-N 5-chloro-n-(2-hydroxy-2-pyridin-3-ylethyl)-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound C=1C2=CC(Cl)=NC=C2NC=1C(=O)NCC(O)C1=CC=CN=C1 ATAGKZOABSLIMT-UHFFFAOYSA-N 0.000 description 1
BRNVNNNLFQUNTP-UHFFFAOYSA-N 5-chloro-n-[2-(4-fluorophenyl)-2-oxoethyl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound C1=CC(F)=CC=C1C(=O)CNC(=O)C1=CC2=CC(Cl)=NC=C2N1 BRNVNNNLFQUNTP-UHFFFAOYSA-N 0.000 description 1
MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 description 1
USQCUKQZXOWUDF-YWZLYKJASA-N 6-chloro-n-[(3s)-1-[(2s)-1-(4-methyl-5-oxo-1,4-diazepan-1-yl)-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]naphthalene-2-sulfonamide Chemical compound O=C([C@@H](N1C([C@@H](NS(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1)=O)C)N1CCN(C)C(=O)CC1 USQCUKQZXOWUDF-YWZLYKJASA-N 0.000 description 1
OBYJTLDIQBWBHM-UHFFFAOYSA-N 6-chloropyridin-2-amine Chemical compound NC1=CC=CC(Cl)=N1 OBYJTLDIQBWBHM-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241001553178 Arachis glabrata Species 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
229940123208 Biguanide Drugs 0.000 description 1
229940122203 Bombesin receptor antagonist Drugs 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
102100024167 C-C chemokine receptor type 3 Human genes 0.000 description 1
101710149862 C-C chemokine receptor type 3 Proteins 0.000 description 1
244000201986 Cassia tora Species 0.000 description 1
208000002177 Cataract Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
108090001085 Cholecystokinin Receptors Proteins 0.000 description 1
102000004859 Cholecystokinin Receptors Human genes 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
102100032165 Corticotropin-releasing factor-binding protein Human genes 0.000 description 1
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 1
108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 1
QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
208000002249 Diabetes Complications Diseases 0.000 description 1
206010012655 Diabetic complications Diseases 0.000 description 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
101100001678 Emericella variicolor andM gene Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
108050001605 Galanin receptor Proteins 0.000 description 1
102000011392 Galanin receptor Human genes 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
102400000321 Glucagon Human genes 0.000 description 1
108060003199 Glucagon Proteins 0.000 description 1
102000030595 Glucokinase Human genes 0.000 description 1
108010021582 Glucokinase Proteins 0.000 description 1
229940121931 Gluconeogenesis inhibitor Drugs 0.000 description 1
239000007995 HEPES buffer Substances 0.000 description 1
241000282412 Homo Species 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
206010022489 Insulin Resistance Diseases 0.000 description 1
102000036770 Islet Amyloid Polypeptide Human genes 0.000 description 1
108010041872 Islet Amyloid Polypeptide Proteins 0.000 description 1
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
108010009384 L-Iditol 2-Dehydrogenase Proteins 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
229920006063 Lamide® Polymers 0.000 description 1
102000016267 Leptin Human genes 0.000 description 1
108010092277 Leptin Proteins 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
239000000867 Lipoxygenase Inhibitor Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
FEYNFHSRETUBEM-UHFFFAOYSA-N N-[3-(1,1-difluoroethyl)phenyl]-1-(4-methoxyphenyl)-3-methyl-5-oxo-4H-pyrazole-4-carboxamide Chemical compound COc1ccc(cc1)N1N=C(C)C(C(=O)Nc2cccc(c2)C(C)(F)F)C1=O FEYNFHSRETUBEM-UHFFFAOYSA-N 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
YNHIGQDRGKUECZ-UHFFFAOYSA-L PdCl2(PPh3)2 Substances [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
108010043958 Peptoids Proteins 0.000 description 1
108010065084 Phosphorylase a Proteins 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920001213 Polysorbate 20 Polymers 0.000 description 1
ZGUGWUXLJSTTMA-UHFFFAOYSA-N Promazinum Chemical compound C1=CC=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZGUGWUXLJSTTMA-UHFFFAOYSA-N 0.000 description 1
LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
208000017442 Retinal disease Diseases 0.000 description 1
206010038923 Retinopathy Diseases 0.000 description 1
108010022999 Serine Proteases Proteins 0.000 description 1
102000012479 Serine Proteases Human genes 0.000 description 1
229910020169 SiOa Inorganic materials 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
102100030980 Sodium/hydrogen exchanger 1 Human genes 0.000 description 1
102100026974 Sorbitol dehydrogenase Human genes 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
229940100389 Sulfonylurea Drugs 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N Tetrahydrothiophene-1,1-dioxide, Natural products O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
108090000190 Thrombin Proteins 0.000 description 1
229940122388 Thrombin inhibitor Drugs 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
DDSWCDPYKYPBBQ-UHFFFAOYSA-N [2-(4-methoxyphenyl)-1,3-dioxolan-2-yl]methanamine Chemical compound C1=CC(OC)=CC=C1C1(CN)OCCO1 DDSWCDPYKYPBBQ-UHFFFAOYSA-N 0.000 description 1
ICPJFOJVDKPEOL-UHFFFAOYSA-N [3-(4-fluorophenyl)-1-(4-hydroxypiperidin-1-yl)-1-oxopropan-2-yl]azanium;chloride Chemical compound Cl.C1CC(O)CCN1C(=O)C(N)CC1=CC=C(F)C=C1 ICPJFOJVDKPEOL-UHFFFAOYSA-N 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000009471 action Effects 0.000 description 1
239000012190 activator Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
108010013985 adhesion receptor Proteins 0.000 description 1
102000019997 adhesion receptor Human genes 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
238000007605 air drying Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003288 aldose reductase inhibitor Substances 0.000 description 1
229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000011609 ammonium molybdate Substances 0.000 description 1
235000018660 ammonium molybdate Nutrition 0.000 description 1
APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
229940010552 ammonium molybdate Drugs 0.000 description 1
239000012378 ammonium molybdate tetrahydrate Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229940125709 anorectic agent Drugs 0.000 description 1
239000000883 anti-obesity agent Substances 0.000 description 1
108010082685 antiarrhythmic peptide Proteins 0.000 description 1
239000003524 antilipemic agent Substances 0.000 description 1
229940125710 antiobesity agent Drugs 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000002830 appetite depressant Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
229960003121 arginine Drugs 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
125000005002 aryl methyl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
FIXLYHHVMHXSCP-UHFFFAOYSA-H azane;dihydroxy(dioxo)molybdenum;trioxomolybdenum;tetrahydrate Chemical compound N.N.N.N.N.N.O.O.O.O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O FIXLYHHVMHXSCP-UHFFFAOYSA-H 0.000 description 1
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 1
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
229960003237 betaine Drugs 0.000 description 1
150000004283 biguanides Chemical class 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
150000001642 boronic acid derivatives Chemical class 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910000024 caesium carbonate Inorganic materials 0.000 description 1
229960001948 caffeine Drugs 0.000 description 1
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 1
229940045200 cardioprotective agent Drugs 0.000 description 1
230000003293 cardioprotective effect Effects 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000013329 compounding Methods 0.000 description 1
239000007891 compressed tablet Substances 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
108010083720 corticotropin releasing factor-binding protein Proteins 0.000 description 1
239000012045 crude solution Substances 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
YYRGUTODIPXGGS-UHFFFAOYSA-N diazepan-5-one Chemical compound O=C1CCNNCC1 YYRGUTODIPXGGS-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
239000002612 dispersion medium Substances 0.000 description 1
239000000890 drug combination Substances 0.000 description 1
239000003596 drug target Substances 0.000 description 1
230000008406 drug-drug interaction Effects 0.000 description 1
238000010410 dusting Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
229940088598 enzyme Drugs 0.000 description 1
238000006345 epimerization reaction Methods 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
KMTPBETYAVWMHD-PPHPATTJSA-N ethyl (2s)-2-amino-3-(4-fluorophenyl)propanoate;hydrochloride Chemical compound Cl.CCOC(=O)[C@@H](N)CC1=CC=C(F)C=C1 KMTPBETYAVWMHD-PPHPATTJSA-N 0.000 description 1
GPZDAOXGEAACMN-UHFFFAOYSA-N ethyl 2-amino-3-oxo-3-phenylpropanoate;hydrochloride Chemical compound Cl.CCOC(=O)C(N)C(=O)C1=CC=CC=C1 GPZDAOXGEAACMN-UHFFFAOYSA-N 0.000 description 1
YUQFHVMIFMXXDW-UHFFFAOYSA-N ethyl 3-(2-methyl-5-nitropyridin-4-yl)-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CC1=CC(C)=NC=C1[N+]([O-])=O YUQFHVMIFMXXDW-UHFFFAOYSA-N 0.000 description 1
JZVWOBCAARHERP-UHFFFAOYSA-N ethyl 3-(3-nitropyridin-4-yl)-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CC1=CC=NC=C1[N+]([O-])=O JZVWOBCAARHERP-UHFFFAOYSA-N 0.000 description 1
ANFSMOBHBMAIKL-UHFFFAOYSA-N ethyl 5-methyl-1h-pyrrolo[2,3-c]pyridine-2-carboxylate Chemical compound CC1=NC=C2NC(C(=O)OCC)=CC2=C1 ANFSMOBHBMAIKL-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000029142 excretion Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000002319 fibrinogen receptor antagonist Substances 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 1
229960004666 glucagon Drugs 0.000 description 1
239000003850 glucocorticoid receptor antagonist Substances 0.000 description 1
229960002442 glucosamine Drugs 0.000 description 1
229960001031 glucose Drugs 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000003979 granulating agent Substances 0.000 description 1
108010093115 growth factor-activatable Na-H exchanger NHE-1 Proteins 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
230000036541 health Effects 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
150000002475 indoles Chemical class 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052816 inorganic phosphate Inorganic materials 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
230000026045 iodination Effects 0.000 description 1
238000006192 iodination reaction Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
208000017169 kidney disease Diseases 0.000 description 1
HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 1
229940039781 leptin Drugs 0.000 description 1
235000014666 liquid concentrate Nutrition 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000006210 lotion Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
LAHWVQFOBUUDBA-VHSXEESVSA-N methyl (2r,3s)-3-amino-2-hydroxy-4-phenylbutanoate Chemical compound COC(=O)[C@H](O)[C@@H](N)CC1=CC=CC=C1 LAHWVQFOBUUDBA-VHSXEESVSA-N 0.000 description 1
PPQSRDMKDFFCIX-QRPNPIFTSA-N methyl (2s)-2-amino-3-pyridin-4-ylpropanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CC1=CC=NC=C1 PPQSRDMKDFFCIX-QRPNPIFTSA-N 0.000 description 1
LAHWVQFOBUUDBA-UWVGGRQHSA-N methyl (2s,3s)-3-amino-2-hydroxy-4-phenylbutanoate Chemical compound COC(=O)[C@@H](O)[C@@H](N)CC1=CC=CC=C1 LAHWVQFOBUUDBA-UWVGGRQHSA-N 0.000 description 1
PPIQQNDMGXNRFA-UHFFFAOYSA-N methyl 2-phenylbutanoate Chemical compound COC(=O)C(CC)C1=CC=CC=C1 PPIQQNDMGXNRFA-UHFFFAOYSA-N 0.000 description 1
RZVWBASHHLFBJF-UHFFFAOYSA-N methyl piperidine-4-carboxylate Chemical compound COC(=O)C1CCNCC1 RZVWBASHHLFBJF-UHFFFAOYSA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000007932 molded tablet Substances 0.000 description 1
MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 description 1
ACYBVNYNIZTUIL-UHFFFAOYSA-N n'-benzylethane-1,2-diamine Chemical compound NCCNCC1=CC=CC=C1 ACYBVNYNIZTUIL-UHFFFAOYSA-N 0.000 description 1
FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
BVRONTVJWFQRME-UHFFFAOYSA-N n-methyl-2-nitro-n-piperidin-4-ylbenzenesulfonamide;hydrochloride Chemical compound Cl.C=1C=CC=C([N+]([O-])=O)C=1S(=O)(=O)N(C)C1CCNCC1 BVRONTVJWFQRME-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
201000001119 neuropathy Diseases 0.000 description 1
230000007823 neuropathy Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000007764 o/w emulsion Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000012285 osmium tetroxide Substances 0.000 description 1
229910000489 osmium tetroxide Inorganic materials 0.000 description 1
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
JMJRYTGVHCAYCT-UHFFFAOYSA-N oxan-4-one Chemical compound O=C1CCOCC1 JMJRYTGVHCAYCT-UHFFFAOYSA-N 0.000 description 1
XHWNEBDUPVMPKI-UHFFFAOYSA-N oxazetidine Chemical compound C1CON1 XHWNEBDUPVMPKI-UHFFFAOYSA-N 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 description 1
AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
HZIVRQOIUMAXID-UHFFFAOYSA-N oxocane Chemical compound C1CCCOCCC1 HZIVRQOIUMAXID-UHFFFAOYSA-N 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000007170 pathology Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
208000033808 peripheral neuropathy Diseases 0.000 description 1
239000012071 phase Substances 0.000 description 1
229940117803 phenethylamine Drugs 0.000 description 1
NCAIGTHBQTXTLR-UHFFFAOYSA-N phentermine hydrochloride Chemical compound [Cl-].CC(C)([NH3+])CC1=CC=CC=C1 NCAIGTHBQTXTLR-UHFFFAOYSA-N 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
125000005543 phthalimide group Chemical group 0.000 description 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
VHBNPKSIIFEKSA-UHFFFAOYSA-N piperidin-4-ylmethylcarbamic acid Chemical compound OC(=O)NCC1CCNCC1 VHBNPKSIIFEKSA-UHFFFAOYSA-N 0.000 description 1
MSDJHYMGDCMMSV-UHFFFAOYSA-N piperidine-2-carboxamide;hydrochloride Chemical compound Cl.NC(=O)C1CCCCN1 MSDJHYMGDCMMSV-UHFFFAOYSA-N 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
229920001184 polypeptide Polymers 0.000 description 1
235000014483 powder concentrate Nutrition 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
238000003672 processing method Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
YDRLUQURTTVLIK-UHFFFAOYSA-N propanal;hydrochloride Chemical compound Cl.CCC=O YDRLUQURTTVLIK-UHFFFAOYSA-N 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000004224 protection Effects 0.000 description 1
239000003801 protein tyrosine phosphatase 1B inhibitor Substances 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
FKSXRCPGQMOMBI-UHFFFAOYSA-N pyridin-4-ylcarbamic acid Chemical compound OC(=O)NC1=CC=NC=C1 FKSXRCPGQMOMBI-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
150000003235 pyrrolidines Chemical class 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
229940076788 pyruvate Drugs 0.000 description 1
230000006340 racemization Effects 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
150000003349 semicarbazides Chemical class 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
230000011664 signaling Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
229910000367 silver sulfate Inorganic materials 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
235000020374 simple syrup Nutrition 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
150000003384 small molecules Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000001420 substituted heterocyclic compounds Chemical class 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
UZSGJDZAMJQCAD-KRWDZBQOSA-N tert-butyl (2s)-2-[(5-chloro-1h-pyrrolo[2,3-b]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)propanoate Chemical compound C([C@@H](C(=O)OC(C)(C)C)NC(=O)C=1NC2=NC=C(Cl)C=C2C=1)C1=CC=C(F)C=C1 UZSGJDZAMJQCAD-KRWDZBQOSA-N 0.000 description 1
YYGUXRWKHHVTSY-CPVNYBHJSA-N tert-butyl (3R)-3-hydroxypyrrolidine-1-carboxylate tert-butyl (3R)-3-methoxypyrrolidine-1-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1C[C@@H](CC1)O.C(C)(C)(C)OC(=O)N1C[C@@H](CC1)OC YYGUXRWKHHVTSY-CPVNYBHJSA-N 0.000 description 1
APCBTRDHCDOPNY-ZETCQYMHSA-N tert-butyl (3s)-3-hydroxypyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@H](O)C1 APCBTRDHCDOPNY-ZETCQYMHSA-N 0.000 description 1
KLKBCNDBOVRQIJ-UHFFFAOYSA-N tert-butyl 4-(aminomethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CN)CC1 KLKBCNDBOVRQIJ-UHFFFAOYSA-N 0.000 description 1
CTMKJUUQPKWNPB-UHFFFAOYSA-N tert-butyl 4-(methanesulfonamido)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(NS(C)(=O)=O)CC1 CTMKJUUQPKWNPB-UHFFFAOYSA-N 0.000 description 1
ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
IRHNQVINMHHEIO-UHFFFAOYSA-N tert-butyl n-(6-chloropyridin-3-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(Cl)N=C1 IRHNQVINMHHEIO-UHFFFAOYSA-N 0.000 description 1
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
DRZYCRFOGWMEES-UHFFFAOYSA-N tert-butyl n-pyridin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=NC=C1 DRZYCRFOGWMEES-UHFFFAOYSA-N 0.000 description 1
RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
229960004559 theobromine Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 description 1
NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
JWCVYQRPINPYQJ-UHFFFAOYSA-N thiepane Chemical compound C1CCCSCC1 JWCVYQRPINPYQJ-UHFFFAOYSA-N 0.000 description 1
XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
AMIGYDGSJCJWSD-UHFFFAOYSA-N thiocane Chemical compound C1CCCSCCC1 AMIGYDGSJCJWSD-UHFFFAOYSA-N 0.000 description 1
125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 description 1
FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
229960004072 thrombin Drugs 0.000 description 1
239000003868 thrombin inhibitor Substances 0.000 description 1
230000000929 thyromimetic effect Effects 0.000 description 1
230000000451 tissue damage Effects 0.000 description 1
231100000827 tissue damage Toxicity 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Diabetes (AREA)
Obesity (AREA)
Endocrinology (AREA)
Cardiology (AREA)
Hematology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Emergency Medicine (AREA)
Vascular Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pyrrole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

NZ543482A 2003-05-21 2004-05-20 Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phoshorylase NZ543482A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US47237503P	2003-05-21	2003-05-21
US55125604P	2004-03-08	2004-03-08
PCT/US2004/016243 WO2004104001A2 (fr)	2003-05-21	2004-05-20	Inhibiteurs d'amide d'acide pyrrolopyridine-2-carboxylique de la glycogene phosphorylase

Publications (1)

Publication Number	Publication Date
NZ543482A true NZ543482A (en)	2009-02-28

Family

ID=33479321

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NZ543482A NZ543482A (en)	2003-05-21	2004-05-20	Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phoshorylase

Country Status (16)

Country	Link
EP (1)	EP1636224B1 (fr)
JP (2)	JP2006528702A (fr)
KR (1)	KR101120935B1 (fr)
AT (1)	ATE473974T1 (fr)
AU (1)	AU2004240946B8 (fr)
BR (1)	BRPI0410445B1 (fr)
CA (1)	CA2525502C (fr)
DE (1)	DE602004028122D1 (fr)
EA (1)	EA009215B1 (fr)
IL (1)	IL171851A (fr)
MA (1)	MA27809A1 (fr)
MX (1)	MXPA05012547A (fr)
NO (1)	NO332265B1 (fr)
NZ (1)	NZ543482A (fr)
UA (1)	UA84146C2 (fr)
WO (1)	WO2004104001A2 (fr)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0205175D0 (en)	2002-03-06	2002-04-17	Astrazeneca Ab	Chemical compounds
GB0205166D0 (en)	2002-03-06	2002-04-17	Astrazeneca Ab	Chemical compounds
US7989634B2 (en) *	2003-11-12	2011-08-02	Lg Life Sciences Ltd.	Melanocortin receptor agonists
JP2007527904A (ja)	2004-03-08	2007-10-04	プロシディオン・リミテッド	グリコーゲンホスホリラーゼ阻害剤としてのピロロピリジン−２−カルボン酸ヒドラジド化合物
EP1732566A4 (fr) *	2004-04-05	2010-01-13	Takeda Pharmaceutical	Compose de 6-azaindole
DE102004054634A1 (de) *	2004-11-12	2006-05-18	Schwarz Pharma Ag	Azaindolcarboxamide
GB0425919D0 (en) *	2004-11-25	2004-12-29	Prosidion Ltd	Indole-2-carboxylic acid amides
PL1819704T3 (pl)	2004-12-02	2008-12-31	Prosidion Ltd	Amidowe pochodne kwasu pirolopirydyno-2-karboksylowego użyteczne jako inhibitory fosforylazy glikogenowej
WO2006059163A1 (fr) *	2004-12-02	2006-06-08	Prosidion Limited	Traitement du diabete par des inhibiteurs de la glycogene phosphorylase
ES2324173T3 (es)	2004-12-02	2009-07-31	Prosidion Limited	Amidas del acido pirrolopiridin-2-carboxilico.
EP1948597A1 (fr) *	2005-10-21	2008-07-30	Vertex Pharmaceuticals Incorporated	Derives modulant des canaux ioniques
BRPI0619985A2 (pt) *	2005-12-16	2011-10-25	Hoffmann La Roche	compostos, processo para a sua manufatura, composições farmacêuticas, métodos para o tratamento e/ou prevenção de enfermidades que estão associadas com a modulação de receptores de h3, de obesidade e de diabetes do tipo ii em um ser humano ou animal e usos dos compostos
PE20110235A1 (es)	2006-05-04	2011-04-14	Boehringer Ingelheim Int	Combinaciones farmaceuticas que comprenden linagliptina y metmorfina
WO2008063842A2 (fr)	2006-11-02	2008-05-29	Aestus Therapeutics, Inc.	Méthodes de traitement de la douleur neuroapathique au moyen d'agonistes de ppar-gamma
FR2911605B1 (fr)	2007-01-19	2009-04-17	Sanofi Aventis Sa	Derives de pyrrolopyridine-2-carbowamides, leur preparation et leur application en therapeutique
DE102007012284A1 (de)	2007-03-16	2008-09-18	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Neue substituierte Arylsulfonylglycine, deren Herstellung und deren Verwendung als Arzneimittel
DE102007035333A1 (de)	2007-07-27	2009-01-29	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Neue substituierte Arylsulfonylglycine, deren Herstellung und deren Verwendung als Arzneimittel
DE102007035334A1 (de)	2007-07-27	2009-01-29	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Neue substituierte Arylsulfonylglycine, deren Herstellung und deren Verwendung als Arzneimittel
DE102007042154A1 (de)	2007-09-05	2009-03-12	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Arylsulfonylaminomethyphosphonsäure-Derivate, deren Herstellung und deren Verwendung als Arzneimittel
US8785489B2 (en)	2008-10-17	2014-07-22	Boehringer Ingelheim International Gmbh	Heteroaryl substituted indole compounds useful as MMP-13 inhibitors
UY32940A (es)	2009-10-27	2011-05-31	Bayer Cropscience Ag	Amidas sustituidas con halogenoalquilo como insecticidas y acaricidas
AR086554A1 (es)	2011-05-27	2014-01-08	Novartis Ag	Derivados de la piperidina 3-espirociclica como agonistas de receptores de la ghrelina
ES2653215T3 (es)	2011-05-31	2018-02-06	Theravance Biopharma R&D Ip, Llc	Inhibidores de neprilisina
JP5959075B2 (ja) *	2011-05-31	2016-08-02	セラヴァンスバイオファーマアール＆ディーアイピー，エルエルシー	ネプリライシン阻害剤
WO2012166389A1 (fr)	2011-05-31	2012-12-06	Theravance, Inc.	Inhibiteurs de néprilysine
IN2015DN01061A (fr)	2012-08-17	2015-06-26	Bayer Cropscience Ag
CN103626825B (zh) *	2013-09-30	2015-10-07	承德医学院	靶向肝脏的糖原磷酸化酶抑制剂胆酸类衍生物、其制备方法及医药用途
CN105829296A (zh)	2013-12-18	2016-08-03	巴斯夫欧洲公司	带有亚胺衍生的取代基的唑类化合物
EP4066896A4 (fr) *	2019-11-27	2024-03-27	Riken	Inhibiteur de g9a
JP7805363B2 (ja)	2020-11-02	2026-01-23	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	ＥＧＦＲ阻害薬としての置換１Ｈ－ピラゾロ［４，３－ｃ］及び誘導体
WO2022192562A1 (fr) *	2021-03-10	2022-09-15	Vincere Biosciences, Inc.	Inhibiteurs d'usp30 et leurs utilisations
CN115894373B (zh) *	2022-10-27	2025-08-01	常州大学	N-取代苄基吡唑衍生物在作为β2肾上腺素受体调节剂、拮抗剂和激动剂的应用
WO2023165168A1 (fr) *	2022-10-27	2023-09-07	常州大学	APPLICATION D'UN DÉRIVÉ DE PYRAZOLE EN TANT QUE MODULATEUR, ANTAGONISTE ET AGONISTE ALLOSTÉRIQUE DU RÉCEPTEUR ADRÉNERGIQUE β2
CN115745891B (zh) *	2022-11-10	2025-08-01	常州大学	吡唑衍生物在作为β2-肾上腺素受体拮抗剂的应用

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4619915A (en) *	1984-10-19	1986-10-28	Pfizer Inc.	Peptide-substituted heterocyclic immunostimulants
IL88619A0 (en) *	1987-12-15	1989-07-31	Pfizer	Non-peptidic renin inhibitors
KR960703856A (ko) *	1994-06-06	1996-08-31	가와노 다케히코	축합 고리를 갖는 카르복실산 화합물, 이의 염 및 이의 약학적 용도(novel fused-ring carboxylic acid compound or salt thereof, and medicinal use thereof)
CA2224062C (fr) *	1995-06-06	2001-09-04	Pfizer Limited	(indole-2-carbonyl-)-glycinamides substitues en n et leurs derives, servant d'inhibiteurs de la glycogene phosphorylase
KR100241643B1 (ko) *	1995-06-06	2000-03-02	디. 제이. 우드	당뇨병치료제인 치환된 N-(인돌-2-카르보닐)-β-알라님아미드 및 그의 유도체
FI974437A7 (fi) *	1995-06-06	1997-12-05	Pfizer	Substituoituja N-(indoli-2-karbonyyli)amideja ja johdannaisia glykogee nifosforylaasi-inhibiittoreina
US5952322A (en) *	1996-12-05	1999-09-14	Pfizer Inc.	Method of reducing tissue damage associated with non-cardiac ischemia using glycogen phosphorylase inhibitors
GB9902047D0 (en) *	1999-01-29	1999-03-17	Cerebrus Ltd	Chemical compounds XI
DE60007592T2 (de) *	1999-09-30	2004-09-16	Pfizer Products Inc., Groton	Bicyclische Pyrrolylamide als Glycogenphosphorylase-Inhibitoren
GB0021831D0 (en) *	2000-09-06	2000-10-18	Astrazeneca Ab	Chemical compounds
GB0202015D0 (en) *	2002-01-29	2002-03-13	Hoffmann La Roche	Piperazine Derivatives
EP1558614B1 (fr) *	2002-10-30	2010-09-01	Merck Frosst Canada Ltd.	Pyridopyrrolizine et derives de pyridoindolizine

2004
- 2004-05-20 MX MXPA05012547A patent/MXPA05012547A/es active IP Right Grant
- 2004-05-20 NZ NZ543482A patent/NZ543482A/en not_active IP Right Cessation
- 2004-05-20 AT AT04753127T patent/ATE473974T1/de not_active IP Right Cessation
- 2004-05-20 AU AU2004240946A patent/AU2004240946B8/en not_active Ceased
- 2004-05-20 DE DE602004028122T patent/DE602004028122D1/de not_active Expired - Lifetime
- 2004-05-20 CA CA2525502A patent/CA2525502C/fr not_active Expired - Fee Related
- 2004-05-20 UA UAA200510756A patent/UA84146C2/ru unknown
- 2004-05-20 EA EA200501645A patent/EA009215B1/ru not_active IP Right Cessation
- 2004-05-20 WO PCT/US2004/016243 patent/WO2004104001A2/fr not_active Ceased
- 2004-05-20 BR BRPI0410445-5A patent/BRPI0410445B1/pt not_active IP Right Cessation
- 2004-05-20 EP EP04753127A patent/EP1636224B1/fr not_active Expired - Lifetime
- 2004-05-20 JP JP2006533345A patent/JP2006528702A/ja not_active Withdrawn
2005
- 2005-11-09 IL IL171851A patent/IL171851A/en active IP Right Grant
- 2005-11-10 NO NO20055305A patent/NO332265B1/no not_active IP Right Cessation
- 2005-11-21 KR KR1020057022252A patent/KR101120935B1/ko not_active Expired - Fee Related
- 2005-11-21 MA MA28613A patent/MA27809A1/fr unknown
2011
- 2011-08-09 JP JP2011174163A patent/JP5669691B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
AU2004240946A1 (en)	2004-12-02
AU2004240946B2 (en)	2011-09-08
CA2525502A1 (fr)	2004-12-02
NO20055305D0 (no)	2005-11-10
WO2004104001A3 (fr)	2005-03-03
EA200501645A1 (ru)	2006-06-30
AU2004240946B8 (en)	2012-01-12
MXPA05012547A (es)	2006-05-25
BRPI0410445B1 (pt)	2017-11-28
CA2525502C (fr)	2012-12-18
IL171851A (en)	2011-08-31
NO332265B1 (no)	2012-08-13
DE602004028122D1 (de)	2010-08-26
JP2011252005A (ja)	2011-12-15
EP1636224B1 (fr)	2010-07-14
BRPI0410445A (pt)	2006-05-30
JP5669691B2 (ja)	2015-02-12
UA84146C2 (ru)	2008-09-25
KR20060069792A (ko)	2006-06-22
EP1636224A2 (fr)	2006-03-22
NO20055305L (no)	2005-12-15
MA27809A1 (fr)	2006-03-01
ATE473974T1 (de)	2010-07-15
JP2006528702A (ja)	2006-12-21
WO2004104001A2 (fr)	2004-12-02
EA009215B1 (ru)	2007-12-28
KR101120935B1 (ko)	2012-03-05

Legal Events

Date	Code	Title	Description
2008-05-30	RENW	Renewal (renewal fees accepted)
2009-06-26	PSEA	Patent sealed
2011-04-29	RENW	Renewal (renewal fees accepted)
2014-05-30	RENW	Renewal (renewal fees accepted)	Free format text: PATENT RENEWED FOR 3 YEARS UNTIL 20 MAY 2017 BY LEA SKYLLERSTEDT Effective date: 20140520
2017-05-26	RENW	Renewal (renewal fees accepted)	Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 20 MAY 2018 BY COMPUTER PACKAGES INC Effective date: 20170502
2018-05-25	RENW	Renewal (renewal fees accepted)	Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 20 MAY 2019 BY COMPUTER PACKAGES INC Effective date: 20180501
2019-11-29	LAPS	Patent lapsed

Publication	Publication Date	Title
CA2525502C (fr)	2012-12-18	Inhibiteurs d'amide d'acide pyrrolopyridine-2-carboxylique de la glycogene phosphorylase
KR102642203B1 (ko)	2024-03-04	급속 진행형 섬유육종 폴리펩티드의 표적화 분해를 위한 다중 고리 화합물 및 방법
US8158622B2 (en)	2012-04-17	Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phosphorylase
KR20240095318A (ko)	2024-06-25	단백질분해 조절제 및 연관된 사용 방법
JP5416710B2 (ja)	2014-02-12	シクロプロピル縮合インドロベンズアゼピンｈｃｖｎｓ５ｂ阻害剤
WO2008072655A1 (fr)	2008-06-19	Dérivés d'imidazothiazole
WO2019015644A1 (fr)	2019-01-24	Composé amide peptidique, son procédé de préparation et son utilisation médicale
WO2011150190A2 (fr)	2011-12-01	Composés inhibiteurs du virus de l'hépatite c (hcv) et leurs procédés d'utilisation
EP1819332B1 (fr)	2009-03-11	Amides d'acide pyrrolopyridine-2-carboxylique
CN113950477B (zh)	2024-07-05	颗粒体蛋白前体调节剂和其使用方法
CN116685576A (zh)	2023-09-01	半胱氨酸蛋白酶抑制剂及其使用方法
CN104884455B (zh)	2017-09-12	丙型肝炎病毒抑制剂
JP2023505485A (ja)	2023-02-09	Ａｔｍキナーゼ阻害剤及び組成物並びにそれらの使用の方法
CN100480249C (zh)	2009-04-22	作为糖原磷酸化酶抑制剂的吡咯并吡啶-2-甲酸酰胺
WO2021132524A1 (fr)	2021-07-01	Dérivé d'époxy azépane
HK40065898A (zh)	2022-08-05	颗粒体蛋白前体调节剂和其使用方法
HK40056262B (zh)	2025-08-01	治疗性化合物